


Gay Story Requests!

by Impastaz



Category: None - Fandom
Genre: Erotica, Gay, Literotica, M/M, Requests, Yaoi
Language: English
Status: Completed
Published: 2019-03-20
Updated: 2019-03-20
Packaged: 2019-11-26 13:31:39
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,523
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18181250
Author URL: https://archiveofourown.org/users/Impastaz/pseuds/Impastaz
Summary: Title is self-explanatory. Mature audiences only! Don’t forget to comment your requests!





	Gay Story Requests!

**Cross Dressing Adventures!**

My name is Alex Rudabaugh. I'm your average teenage girl. I'm shy, and I love fashion and makeup. But there's just one problem. I have a penis.  
I started cross dressing when I was eight. I would put on my sisters dresses, wear lip gloss, and would admire myself in the mirror. When Mom and Dad found out, they were worried, but supportive. I was bullied a lot. Kids would call me a sissy, a pervert, all kinds of awful names. It's one of the reasons why we moved. But it was the perfect opportunity to become one with my lifestyle, and I began to crossdress at school! I was so nervous at first. It felt so weird to walk in the halls, wondering if anyone would find out I was a boy. But there was also a sense of excitement in the danger. I never realized just how "excited" I could be until one warm spring day...  
It was going to be a big step for me. Without Mom or Dad knowing, my sister had taken me to get a few pairs of panties, the soft silky kind. I felt so sexy and feminine in them! In a bold move, I wore them to school.  
As I walked in the halls, I could feel the soft material rubbing against me. I couldn't help but begin to get hard. I quickly rushed into the girls bathroom, locking myself in the last stall. I pulled down my panties and inwardly groaned. They were soaked with precum! There was no way I could walk around in them... And I couldn't call Mom or Dad... I quickly stuffed them into my book bag, pulled up my pants and skirt, and shakily stepped out of the bathroom.  
"Hey Alex!"  
I flinched and turned around.  
"O-oh! Hi, M-M-Mark!"  
Mark was the best player on the football team. He was tall, athletic, and blessed with baby blue eyes, full lips that were just begging to be kissed... And his hair... His silky blonde locks were like an angel's. And there he was, standing right in front of me!  
"The movie theater is showing Pet Sematary this weekend, and I have an extra ticket." He smiled, showing his perfect white teeth. "It would be really cool if you would go with me."  
I felt a rush of heat go through my body. The hottest guy in school wanted to go on a date?! With me?! But...  
"Oh... Th-this weekend? I'm sorry... I have to watch my nephew that day..."  
I felt terrible for lying to him. But I knew that if he found out who I really was, he would be mortified. My heart shattered as his smile dropped.  
"Oh. Well, that's okay, I guess... I'll just take my dad with me. It's good to have guy time, anyway." He paused, then smiled again. "You would know a thing or too about that, huh?"  
I froze, a cold chill going down my spine. I desperately tried to play it cool.  
"Y-yeah, r-right, sure..."  
_Oh my god, he knows!!!_  
"Meet me behind the bleachers after school, okay? There are some things we need to talk about."  
Who was I to refuse? Who knew what he would do if I said no!  
"O-okay," I said, trembling.  
He patted my shoulder, surprisingly chipper.  
"See ya then!"  
I could hardly focus on your classes for the rest of the school day. My heart was constantly hammering in my chest, and my palms were unbearable sweaty. I kept wondering what he would say or do. Probably blackmail me for money or homework...  
The bell rang all too soon, and I quickly grabbed my things, heading out the classroom door. Next stop, the bleachers...  
It was a warm day, but I was shivering as you waited by the bleachers. I was so nervous...  
"I didn't think you'd come."  
I let out a shrill yelp and whipped around. There he was, grinning like a fox.  
"That was a cute little sound."  
My face reddened, but I refused to give in.  
"Wh-what do you want, M-Mark? What do you know?!"  
Mark raised his hands defensively.  
"Whoa, hey, chill out, man." He paused. "That's what you are, isn't it?"  
Tears stung in my eyes, and I clenched my fists, defeated.  
"Yeah. Yeah, I am. What are you gonna do? Tell everyone? Blackmail me? Bully me?!"  
Mark eyes softened.  
"No. No, I'm not."  
I looked away, trying not to let him see the tears falling down my cheeks.  
"Hey, hey..." Mark's voice was calm and comforting. "I'm not going to hurt you. I'm not going to bully you. Alex, I knew right from the start that you were a guy. I'm pretty sure everyone knows."  
I groaned, covering my face with my hands.  
"Is it that obvious...?"  
Mark chuckled, then gently took my hands away from my face, looking at me in the eyes.  
"Nah. A few things tipped me off. How many times you accidentally went into the boys restroom, the way you would try to move your..." He gave a quick glance down. "When you got uncomfortable. Which makes me wonder..."  
His gentle hands trailed up my arms, then down over my chest and waist. I felt goosebumps rise up on my arms and legs, and I shuddered.  
"What's going on down here...?"  
I gasped as Mark lifted up my skirt and pulled down my tights in one fluid movement. He looked down at me, his eyes filled with passion and lust.  
"What's this, huh?"  
I was completely erect, my leaking member begging for attention. I covered my eyes.  
"Eh?! Wh-what are you-?!"  
"Hush."  
His lips pressed against mine, effectively silencing me. I locked up, then remembered to at least try to move my lips. I wanted my first kiss to be a good one. It was sloppy and unexperienced, but I couldn't help but moan as he slipped his tongue between my lips. His hand found the back of my head, and he ran his fingers through my hair. His other hand grabbed my waist, pulling it forward so that my naked cock pressed against his jeans. I blushed as I felt how rock hard he was. I forced myself to break the kiss, and I realized that I was gasping. It was like I had completely forgotten how to breathe.  
"Mark, I... Why would you...?"  
He gave my ass a quick squeeze, and I yelped, pressing closer to him.  
"You're irresistible, Alex." He kissed me again, desperate and feverish. "Come home with me today. Let me show you just how much I've been wanting you."  
I nodded without a second thought. 

As we rode in his red convertible, I admired the spotless leather seats. For a jock, he was surprisingly neat. I felt like I had to pay money just to sit in such a luxurious car. I sighed as I felt the cool breeze whip through my hair, a few rebellious strands tickling the sides of my face.  
"You look amazing right now, Alex," Mark said, gazing at my through his sunglasses. "I can hardly believe it. Such a pretty thing like you sitting right here in my car..."  
I looked away, blushing deeply. I had never heard such a compliment before. I flinched as I felt his strong hand rest on my thigh, and my dick twitched up, interested.  
Stay down, damn you!  
"Almost there," Mark assured me, a hint of amusement in his voice.

His house was very much like his car, expensive-looking and very clean.  
"My folks won't be here for another week, so we're all alone right now."  
He grabbed my arm, then turned me around skillfully, bringing me to his chest. I could feel his erection straining against his pants, poking into me.  
"Is that a banana in your p-pants, or are you just happy to see me?"  
_Fuck._  
I cringed at my god-awful joke. I couldn't think of anything to say!  
"I'm very happy to see you, Alex." He dipped down so that his mouth was close to my ear, his warm breath tickling my skin. "Very happy."  
His voice was a deep, rumbly purr, and it turned me on like nothing else. I exhaled sharply as I shuddered, leaning my head back and exposing my neck. I hoped he would accept the invitation. He seemed to get the message, and wasted no time in placing his lips down on my neck. My eyes rolled back a little, my knees weakening. He attacked my sensitive skin with his lips and tongue, his hands everywhere, groping and squeezing. I was painfully hard by now. I swallowed nervously.  
"M-Mark?"  
"Yes?" He said breathily, running his hands up and down my waist.  
"P-p-please touch me."  
He paused.  
"I am touching you, baby."  
I could practically hear his smile. If that was even possible.  
"I-I mean, c-can you..."  
I summoned my courage and took his hand, guiding it down to the front of my skirt. With my other hand, I lifted it up and pulled down my tights, revealing my small erection.  
"Touch me here...?"  
His lips barely brushed against my ear. His fingers were dangerously close.  
"You want me to touch your cock, sweetheart? You want me to make you feel good?"  
I fell apart at his words.  
"Yes! God, please, Mark, please touch me, please!"  
I was mindlessly begging now.  
"Alright."  
All it took was a simple touch to make me gasp, my fingers clutching his arm. His index finger rubbed at the head, spreading my precum all around it. It felt so different from the times I would touch myself. I was already at the brink of cumming when he closed his hand around my cock, slowly pumping it as though it was something precious and delicate. I couldn't stop myself as I began to thrust into his fist, my mind completely blank from the pleasure. It was a warm, soft friction covering me entirely, sending electricity all the way up my spine and down to my toes. It felt like nothing I had ever experienced.  
"You like that, sweetheart? You like it when I touch you like this?"  
I nodded dumbly, practically mute from the pleasure. My lips parted, but no sound came out, other than small choked noises. The silence was broken when he rubbed at the head again, moving his hand faster. I let out a loud, embarrassing moan, and I covered my mouth in shame. Mark was quick to pull my hand down.  
"No. I wanna hear you. Show me how good I'm making you feel."  
My cheeks were burning, and I moaned again as he gently squeezed me.  
"God, you're turning me on so much..."  
His pace became tougher and faster, and he began to grind into my behind, burying his face in my hair. A beautifully hot pressure began to build up inside me, and I felt my balls began to tighten.  
"W-wait, Mark, wait!"  
In an instant, his hands were off me.  
"What's wrong?" He asked anxiously. "Did I hurt you?"  
I turned around and smiled at him reassuringly.  
"No, no, I'm fine. I just didn't want it to end yet. Maybe..." I cleared my throat. "I was hoping that maybe we could take it to your room?"  
His worried frown broke into a wide grin, and my heart fluttered, even as my dick throbbed painfully from the denied orgasm.  
"Yeah. Come on, follow me."  
He led me to his room, where he took my hand and guided me to the bed. He laid me down carefully, treating me as though I was made of porcelain. His lips met mine, but it wasn't hungry and animalistic like our previous kisses. It was soft, tender, and loving. I was shocked by the sudden gentleness. I closed my eyes and leaned into it, letting him lead. It was exactly like the stories that my girl friends would tell me about their first kisses, how it was like magic and fireworks. But I never expected it would leave me so dizzy and breathless, though it was in the best way. He eventually pulled away, and I looked down. He hadn't calmed down in the slightest, and I knew that it had to be painful. With trembling hands, I grabbed the front of his pants and unbuttoned them. He watched wordlessly, impressed by my bold move. I pulled down the zipper, and he did the rest, sitting up and pulling his pants and undergarments down. My eyes widened as his cock was revealed. It bounced as it was freed from its confinements, and I couldn't help but notice how mine was pathetically small compared to his. It was actually rather intimidating... But I couldn't tear my eyes away. The tip was perfectly puffy, the hardness giving it a raging red appearance. A thick vein ran from the head down to the shaft, which was impressively thick.  
"Like what you see?"  
I snapped out of my trance, looking up at him.  
"V-very much," J admitted shyly. "C-can I...?"  
Mark playfully raised an eyebrow.  
"Can you?"  
Ugh! He knew what I was trying to ask! I swallowed my nervousness and spoke.  
"Can I... Can I t-touch it?"  
He smiled, pleased.  
"Yes, baby."  
I sat up, then hesitantly reached down, putting my small hand around him. I tried my best to reciprocate what he had done to me earlier. My technique was pathetically weak, but he closed his eyes and hummed in approval. Precum sprouted at the tip, and I suddenly felt a driving curiosity as to what it tasted like. Not asking for permission, I leaned down and licked it up. Mark stiffened, inhaling sharply. The taste was salty, slightly bitter, but I wanted more. I squeezed his cock, careful not to hurt him, then licked all around the head, coating it in saliva. Mark let out a long deep moan that made me shudder, and I felt encouraged. It felt good to make him feel pleasured too. I forced myself to fit more into my mouth, cautiously avoiding my gag reflex. I began to bob my head, the way I had seen the "adult film" stars do. Mark groaned, putting his hand on my head and petting my hair.  
"F-fuck... Alex..."  
My tongue found the vein, and I began to trace and lick at it. I had the pleasure of feeling him twitch in my mouth. I barely even had a third of him inside me, but what I couldn't fit in my mouth, I worked with my hands, rubbing and squeezing as best as I could.  
"You're doing so good, sweetheart," Mark panted. "Atta girl."  
His words sparked a change in me. I pulled off of him with a lewd popping sound, then began wildly licking him up and down, my hand massaging and fondling his neatly trimmed sack. He grunted at the sudden flip, clutching the bedsheets as I assaulted him with my tongue. I didn't leave an inch of him untasted. I began to grind against the bed, looking up at him innocently. His face was contorted in pleasure, a small bead of sweat running down his temple. He noticed my look, and he groaned at the sight of me staring up at him while I did such a naughty thing.  
"I can't... Fuck, baby, I can't!"  
I gasped as he grabbed my shoulders, flipped me over, then pinned me down on the bed.  
"It's about time I got a taste of that sweet ass."  
I was helpless as he lifted up my waist, then pulled down my skirt and tights. His strong hands grabbed my behind, spreading the cheeks apart.  
"M-Mark," I whimpered, "p-p-please don't look there, it's...!"  
"Sexy as hell, I know."  
Before I could protest, I felt something wet quickly run all the way up from my perineum to the top of my behind. My back arched as I let out a shocked yelp.  
_Is that...?!_  
I got my answer as he attacked me again, and I could feel the stubble on his face against my ass as his tongue lapped against my hole. My body convulsed violently at the new, strange sensation. He was seriously eating me out!  
"M-Mark, you c-c-can't! It's g-gross and d-d-dirty back there!"  
The tip of his tongue prodded against me, and my body tensed, tightening up against the invader. Nonetheless, he worked his way inside, wiggling and thrusting his tongue. He let out a throaty groan, as if he was eating something delectable. The vibrations from his voice sent me over the edge, and I pushed my ass back into his face, crying out in pleasure. His fingers dug into the meaty flesh as he licked and sucked at my hole with aggressive vigor.  
"Oh G-God, Mark, your t-tongue feels so f-fucking good!"  
I was going crazy from the amazing sensation, precum and saliva dripping down onto the bed from his ministrations. His tongue was amazing, but I badly wanted something bigger.  
"Fuck me!" I suddenly cried out.  
I froze. Did I really say that?! In an instant, Mark's tongue was gone, and he had flipped me back over. I looked down, where he was slowly jerking himself.  
"You want this?"  
I nodded wordlessly, my eyes fixed on his cock.  
"Yeah? You want this inside you, baby?"  
I nodded again, more desperately.  
"P-please, Mark. I n-need you!"  
He grinned, then stroked my cheek lovingly.  
"We gotta stretch you out first. I don't want to hurt such a pretty thing like you."  
I groaned in disappointment, but I knew he was right. He would probably kill me if he put it in now! I watched as he opened his mouth, letting a generous amount of spit fall onto his fingers. He looked up at me.  
"Are you ready?"  
I was confident enough to use my words this time.  
"Y-yes. I'm ready."  
"Good."  
I stiffened as he reached down, his fingers rubbing against my ass. He spread his saliva around, then began to push his middle finger into me. My hole immediately clenched and relaxed, trying to push out the foreign object. Mark's lips twitched as he felt my contacting muscles around the digit. He kept it in, occasionally twisting it gently to keep me interested. I almost felt tempted to move my hips, to get some kind of action going, but I didn't want to rush him. He seemed to know what he was doing. After a painfully long period of slightly twitching and twisting, he spoke.  
"I'm gonna move it now, okay? If it hurts too much, just tell me."  
He pulled his finger out, then slooowly forced it back in, all the way to the last knuckle. I let out a quiet hiss in discomfort, but thanked my lucky stars that I had a "cleansing day" just the day before.  
"Nice and clean, huh? I bet you've been wanting something like this to happen."  
I blushed madly.  
"I-I wasn't expecting this! I just try to keep clean, th-that's all."  
I appreciated him trying to take my mind off the discomfort, but such a sudden object in me was hard to ignore. He managed to push in a little deeper, then he just barely curled his finger. A sudden shock of pleasure shot through my body from deep inside me, and I shouted, startled. Mark chuckled deviously.  
"Gotcha."  
He pressed against that spot again, and I yelped again, grabbing onto the sheets for dear life.  
"Wh-what are you doing?! Why am I...?"  
"That's your prostate, Alex. Your 'feel good spot.'"  
"O-oh."  
_God, I'm so lame._  
I convulsed, my eyes rolling back as he stimulated me again and again, and I barely noticed that he had slipped in a second finger.  
"That should do it. Don't want you to be too loose, now."  
He spit into his hand again, slathering it onto his dick.  
Oh god, this is really happening... The coolest, hottest guy in school is about to have sex with me?  
"W-wait," I said.  
He stopped, looking down at me with worry.  
"What's wrong? Did you change your mind?"  
"No!" I blurted. "No, absolutely not, I just..." I sighed shakily. "I-I just need to know what this will m-mean. Like, is it gonna be a one time thing? Are we gonna be friends with b-benefits, or... Are we gonna date or something...?"  
Mark smiled, petting my hair.  
"Is that what you want?"  
I nodded shyly.  
"I just want to know if you feel the same way I do..."  
Mark seemed shocked.  
"Alex, I took you into my home, kissed you, touched you in a way I've never touched anyone before. And yes, I'm a virgin. I may look alike a sex demon, but I'm as new to this as you are." He smiled, looking into my eyes. "Do you really think I would do all of this if I wasn't absolutely crazy about you? You're smart, cute, and just totally amazing. I've wanted you since I first saw you. And this isn't just about your body, even though you're absolutely sexy." I blushed at that, shaking my head. "And don't even deny it! I love you for you. I have since the beginning. And if you feel the same way, then I would be proud to have you as my girlfriend. I'll support you, buy you clothes, bring you home and cook you dinner, anything you want." His cheeks reddened. "And I'm ranting now. But I want you to know that I want more from this. I want you, Alex."  
By then, tears were streaming down my face. I smiled brightly.  
"Then take me, Mark." My voice was calm and steady for the first time, not stuttery and anxious like before.  
"I will. I love you, Alex."  
I reached down, taking him in my hand and guiding him to my hole.  
"I love you too, you stud."  
He gave me a breathtaking grin, then pressed his lips to mine lovingly. I stiffened as the head of his cock pressed up against me, then it breached, slipping into me. I saw fireworks behind my eyes. The stretch was incredible. There was no way he was going to fit! My hole burned as he seemed to split me apart, and I clutched his shoulders, my nails digging into his skin.  
"S-stop," I choked. "M-Mark, fuck... Stop, please..."  
He paused, wiping the sweat from my forehead.  
"It's alright, baby... We'll take it easy, okay? But you gotta relax. You're tensing up too much, and that's what's making it hurt so much."  
I didn't even realize how frozen I was. I let out the breath I didn't know I was holding, hissing through my teeth. I forced myself to relax, and the pain subsided to a tolerable dullness.  
"Atta girl, there we go..."  
He pushed in a fraction of an inch more, taking his time.  
"Just breathe, baby, breathe..."  
My death grip on him lessened, and I audibly sighed in relief as I felt the base of him press against my bottom.  
"See? All in. Wasn't that bad, was it?"  
I smiled at him, wiping away the tears that were gathering in the corners of my eyes with a giggle.  
"It's... It's really big, Mark."  
He rolled his eyes, but I saw his pleased blush.  
"It ain't nothing special. But yours..."  
I moaned in surprise as he grabbed my dick, wasting no time as he stroked it. He slightly pulled out, then pushed right back in, the head of his member lightly brushing against my prostate. It was faint, but it still sent a pleasurable shiver through my body. I wanted more.  
"F-faster," I whispered. "You can go faster. Please."  
Mark kissed my forehead.  
"Your wish is my command, baby."  
He quickened his pace, grabbing my legs and lifting them to get better access. He hit even deeper, pushing up against my sweet spot. I let out a high pitched moan, and he took the opportunity to bend down and capture my mouth with his, forcing his tongue past my lips. We kissed passionately, the only sounds in the room being our labored breathing, moans, and the soft squelching sounds as he fucked me. I squirmed beneath him, wanting more.  
"Tell me what you want, baby. You want me to go faster? You want me to pound your little pussy?"  
His dirty talking made my cock twitch, and I nodded desperately.  
"Yes, Mark, fuck me harder, please! Make my ass yours, take me!"  
I could hardly believe the naughty words coming out of my mouth. He was making me into a total slut! I screamed as he thrusted into me roughly, his cock brutally stabbing into me. A tiny spurt of precum dribbled onto my stomach, and Mark swiped it up with his finger, putting it into my mouth.  
"Here, taste yourself."  
I sucked on the digit obediently, moaning at the taste. It was more bitter than his, but the saltiness was there. He thrusted sharply again, and my back arched as I cried out, my hole tightening around him. He grunted.  
"God damn... If you keep being this tight, I'm gonna blow right away!"  
That made me happy, hearing that. It meant that I was making him feel as good as he was making me. I was ready to burst too. But I wanted this to last as long as it could! He kept up his brutal pace, pulling out until all but the tip was out, then crashing back in. He would rotate and shake his hips, making me feel every inch of him. Every thrust was bringing me closer and closer to my orgasm, and I could tell he was reach his limit as well. He was perspiring, small beads of sweat running down his defined chest and stomach. His crystal blue eyes were rolled back, and I knew he was as lost in the pleasure as I was. His breathing suddenly became ragged, and his thrusts were erratic and stuttering. He was right at the edge, and I would be right there with him. I reached down and grabbed my cock, and it took only a few strokes before my orgasm hit me like a train. Mark's hard, rough thrusts, the sight of his gorgeous body, and the friction of my hand shoved me over the edge. Ropey streaks of cum splattered onto my stomach and chest, my hole contracting rhythmically. The tightening must have pushed Mark, too, because he let out a thunderous moan as he shuddered. His cock twitched, and I felt a warm wetness spreading inside me. He thrusted once more, then pulled out, his cum leaking out of my now-empty hole. I felt disappointingly empty, but I forgot about it when I saw Mark's exhausted but satisfied face.  
"That was... Holy fuck, Alex..." He looked down at the mess we made, grinning. "Come on, let's get you cleaned up."

About an hour later, we were on the road again, and I was gingerly shifting in the seat, careful to avoid sitting the wrong way. My ass was going to be sore for a while...  
"So, about that movie..."


End file.
